Development of the BIPI ligands for asymmetric hydrogenation

Carl A. Busacca; Jon C. Lorenz; Anjan K. Saha; Sreedhar Cheekoori; Nizar Haddad; Diana Reeves; Heewon Lee; Zhibin Li; Sonia Rodriguez; Chris H. Senanayake

doi:10.1039/C2CY20337E

Development of the BIPI ligands for asymmetric hydrogenation†

Carl A. Busacca,*^a Jon C. Lorenz,^a Anjan K. Saha,^a Sreedhar Cheekoori,^a Nizar Haddad,^a Diana Reeves,^a Heewon Lee,^a Zhibin Li,^a Sonia Rodriguez^a and Chris H. Senanayake^a

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^a Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Rd., Ridgefield, USA
E-mail: carl.busacca@boehringer-ingelheim.com
Tel: 001 203-798-4126

Abstract

The detailed development of unique BIPI ligands suitable for asymmetric hydrogenation is described, and the process research leading to their kilogram-scale manufacture is discussed. Full optimization of each ligand region is shown, and the complete design features for these ligands are explained. Application of the best members of this ligand class to asymmetric hydrogenations of ureaesters, BOC- and CBZ-enecarbamates, and a variety of enamides are described. A novel resolution of P-chiral ligand precursors via their zinc complexes is described, and the research leading to the discovery of catalysts capable of carrying out asymmetric hydrogenations in >99% ee at multi-kilogram scale are presented.

This article is part of the themed collection: Homogeneous and heterogeneous catalysis in industry

Catalysis Science & Technology

Development of the BIPI ligands for asymmetric hydrogenation†

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Development of the BIPI ligands for asymmetric hydrogenation

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